321863-61-0

Usage

Uses

Used in Organic Synthesis:
(alphaS)-alpha-Cyclopropylbenzenemethanamine is used as an intermediate in organic synthesis for the production of various chemical compounds. Its unique structure allows for selective reactions and the formation of complex molecules with potential applications in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (alphaS)-alpha-Cyclopropylbenzenemethanamine is utilized as a key intermediate in the development of new drugs. Its chiral nature and reactivity make it a valuable building block for the synthesis of biologically active molecules, including potential therapeutic agents.
Used in Laboratory Research and Development:
Due to its structural features and synthetic potential, (alphaS)-alpha-Cyclopropylbenzenemethanamine is widely used in laboratory research and development processes. It serves as a model compound for studying various chemical reactions and exploring new synthetic pathways, contributing to the advancement of chemical science.
Used in Chemical Production Processes:
(alphaS)-alpha-Cyclopropylbenzenemethanamine is also employed in chemical production processes, where it is transformed into other valuable chemicals or materials. Its versatility and the ability to undergo various reactions make it an essential component in the chemical manufacturing industry.

Synthesis

A solution of (S)-2-amino-3-methyl-1,1-diphenylbutan-1-ol (47 mmoL 12 g) in THF (80 mL) was stirred at temperature below 30 °C. followed by slow addition of borane-tetrahydrofuran solution (1M, 95 mL). The tempera-ture was allowed to rise to room temperature over 2 h, The reaction mixture was then stirred at 0 °C. and the solution of pure anti-cyclopropyl(phenyl)methamine-benzyl oxime (19 mmol, 5 g), in THF (10 mL) was added. After stirring the mixture for 20 h at room temperature, the reaction mixture was cooled to 0 °C. and treated with hydrochloric acid (2N, 100 mL). The mixture was stirred for 16 h then basified at 0 °C. by addition of 35% sodium hydroxide (100 mL) followed by extraction with ethyl acetate. Extract washed with water and brine, dried over sodium sulfate and evaporated to dryness. Amine was purified by LC (BIOTAGE SPI purification system), using chloroform:methanol (gradient up to 25% of methanol) to give 2.1 g of (S)-cyclopropyl(phenyl)methanamine, yield 72%.

Upstream product

• 7555-72-8 cyclopropyl(phenyl)methanone oxime 
• 64-17-5 ethanol 
• 23719-80-4 cyclopropylmagnesium bromide 
• 100-47-0 benzonitrile 
• 3481-02-5 cyclopropyl phenyl ketone 
• 1133706-10-1 C₁₈H₃₁NOSi 
• 4333-56-6 cyclopropyl bromide 

Downstream Products

• 100390-22-5 (cyclopropyl-phenyl-methyl)-carbamic acid methyl ester 
• 74787-86-3 3-(Cyclopropyl-phenyl-methyl)-1-(2-hydroxy-ethyl)-1-methyl-thiourea 
• 1376352-76-9 C₁₃H₁₉NO₃S 
• 1376332-88-5 N-(cyclopropylphenylmethyl)methanesulfonamide 
• 1376394-94-3 C₁₇H₂₅NO₂S 
• 1338793-54-6 N-(cyclopropyl(phenyl)methyl)-3-(3-sulfamoylphenyl)-1H-indazole-5-carboxamide 
• 73611-78-6 (Z)-(4-bromobut-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Method for synthesizing chiral amine compound

The present invention provides a method for synthesizing a chiral amine compound. The method comprises the following steps: (1) reacting a compound of formula I with t-butylsulfonamide in the presenceof a catalyst to obtain a compound having a structure represented by formula II; 2) reacting the compound of the formula II in a hydrogen atmosphere in the presence of an iridium catalyst and a ligand to obtain a compound of formula III; and (3) carrying out a t-butylsulfonyl group removal reaction on the compound of the formula III to obtain the chiral amine compound. The method constructs the structure of sulfonamide by a keto carbonylgroup, and synthesizes the chiral amine compound with the aralkylamine structure by an asymmetric catalytic hydrogenation reaction of the sulfonamide structure, the ee value is generally 80% or above, the highest ee value is 99% or above, the yield of each step reaction can reach 90% or above, and the total yield is high.

A JAK/STAT3 phosphorylation inhibitor and its preparation method and use thereof

The invention provides a JAK/STAT3 phosphorylation inhibitor as well as a preparation method and application thereof. The structural formula of the JAK/STAT3 phosphorylation inhibitor is as shown in a formula I, wherein X is selected from S or O; Y and Z

New quinoline NK3 receptor antagonists with CNS activity

Lead optimisation starting from the previously reported selective quinoline NK3 receptor antagonists talnetant 2 (SB-223412) and 3 (SB-222200) led to the identification of 3-aminoquinoline NK3 antagonist 10 (GSK172981) with excellent CNS penetration. Investigation of a structurally related series of sulfonamides with reduced lipophilicity led to the discovery of 20 (GSK256471). Both 10 and 20 are high affinity, potent NK3 receptor antagonists which despite having different degrees of CNS penetration produced excellent NK3 receptor occupancy in an ex vivo binding study in gerbil cortex.

Orally Bioavailable Caffeic Acid Related Anticancer Drugs

The present invention concerns compounds and their use to treat cell proliferative diseases such as cancer. Compounds of the present invention display significant potency as inhibitors of Jak2/STAT3 pathways and downstream targets and inhibit the growth and survival of cancerous cell lines.

Substituted pteridines for the treatment of inflammatory diseases

The invention relates to new pteridines which are suitable for the treatment of respiratory or gastrointestinal complaints or diseases, inflammatory diseases of the joints, skin or eyes, diseases of the peripheral or central nervous system or cancers, as

THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS

Disclosed are novel compounds of the formula (IA) and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula (IA).

3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands

There are disclosed compounds of the formula or a pharmaceutically acceptable salt or solvate thereof which are useful for the treatment of chemokine-mediated diseases such as acute and chronic inflammatory disorders and cancer.

Influence of bulky substituents on histamine H3 receptor agonist/antagonist properties

Novel derivatives of 3-(1H-imidazol-4-yl)propanol were designed on the basis of lead compounds belonging to the carbamate or ether series possessing (partial) agonist properties on screening assays of the histamine H3 receptor. One pair of enantiomers in the series of α-methyl-branched chiral carbamates was stereoselectively prepared in high optical yields. Enantiomeric purity was checked by Mosher amide derivatives of precursors and capillary electrophoresis of the final compounds with trimethyl-β-cyclodextrin as chiral selector, and was determined to be ≥95%. The novel compounds were investigated in various histamine H3 receptor assays in vitro and in vivo. Some compounds displayed partial agonist activity on synaptosomes of rat brain cortex, whereas others exhibited antagonist properties only. Selected compounds were investigated in [125I]iodoproxyfan binding studies on the human histamine H3 receptor and showed high affinity in the nanomolar concentration range. Under in vivo conditions after oral administration to mice, some of the compounds exhibited partial or full agonist activity in the brain at low dosages. The (S)-enantiomer of one pair of chiral carbamates (9) proved to be the eutomer; thus, the (S)-enantiomer was selected for further pharmacological studies. In a peripheral in vivo test model in rats, measuring the level of inhibition of capsaicin-induced plasma extravasation, (S)-9 again proved its high oral agonist potency with full intrinsic activity (ED50 values of 0.07-0.1 mg/kg depending on tissue).

Branched alkylamino derivatives of thiazole, processes for preparing them and pharmaceutical compositions containing them

The invention relates to the derivatives of formula I: STR1 in which R1 represents a phenyl or naphthyl radical (optionally substituted), R2 represents a hydrogen or halogen atom or an alkyl, hydroxymethyl or formyl radical, R3